For as ground-breaking a show as Friends was, being the last true gasp of network television dominance before the cable revolution started halfway through the show’s run, some parts of the show have aged about as well as a milk carton left out on the kitchen counter. All six of the titular friends could be awful to one another, toeing the line between playful bickering and legitimate cruelty, sometimes stepping over that line entirely.
Throughout the ten seasons and 200+ episodes, Monica, Rachel, Ross, Phoebe, Joey, and Chandler each had their share of fumbles, often silly little mistakes that create the standard sitcom fodder. Yet, occasionally, there is a nugget of cruelty underneath that shows how far the lovable 90s icons can take something.
6 Monica: Accusing (and Sexually Harassing) the Maid
In “The One with the Stain," Monica and Chandler’s new maid Brenda comes under Monica’s fire when Brenda wears a pair of jeans that is similar to a pair Monica recently lost. Distrustful and paranoid, Monica notes that her pair had an ink stain in the crotch of the jeans, so after an attempt to leer and get a very good view of the stained area—a joke that is especially uncomfortable nowadays—she sends Chandler after the maid.
While watching Chandler bumble through hitting on a stranger is funny for a moment, it reveals a much darker impulse when analyzed further. Monica’s obsessive assumption that everyone is out to get her and dethrone her is already a tad concerning when it comes to her friends, but when she brings in strangers to her ego games, the results become less funny and more upsetting.
5 Phoebe: Various Crimes
Phoebe’s made no secret of her criminal past, but the details of her past are so vague and unconfirmed that it’s hard to pinpoint her worst moment. The revelation that she mugged Ross back before they were friends was bad enough, but, over the years, Phoebe sprinkled little tidbits of her past into everyday conversation.
How vague these tidbits can be make it hard to pinpoint one as Phoebe’s worst moment, and Phoebe is the least reliable character on the show when discussing her past, but there are a few doozies. One of the worst ones was the time she stabbed a police officer, after “he stabbed [her] first." There’s no further mention of this in the show, but the mysterious vegetarian has made multiple references to a long criminal record, and possibly a body count.
4 Chandler: Kissing One of Joey’s Sisters… And Then Forgetting Which One
Chandler has a relatively strong head on his shoulders for being one of the Friends. He’s the only guy of the group to have a stable relationship, he’s loyal, and he’s good enough at his job that the show never actually explains what it is he does.
But, before that aforementioned relationship, at Joey’s birthday party in season three, Chandler gets plastered and kisses one of Joey’s seven sisters who all look very similar. After leading Joey to believe he may be in love with the sister to try and save face, Chandler attempts to smooth things over with the sister, but he ends up kissing her again. As he does this, the sister he actually kissed walks in; Chandler was smoothing things over with the wrong one.
Chandler is rarely consciously cruel, but he can be very stupid. This blunder, as well as how poorly he tried to dig himself out of it, is a clear example of that.
3 Joey: Saving a Sandwich Over His Friends
Joey Tribbiani’s flaws mostly come with him being spectacularly dumb; from his failed attempts to create an acting career to dropping his pants on his first meeting with Monica after she “invited him in for lemonade," there are a lot of stupid moments in Joey’s life.
Yet, the pinnacle of Joey’s… well, "Joeyness" comes in the episode “The One with the Ride-Along," where Joey, Ross, and Chandler are in the backseat of a cop car doing a ride-along. The car backfires, and Joey, thinking the sound is a gunshot, leaps over Ross to protect him. This causes a rift between Joey and Chandler before Joey reveals that he didn’t want to save either of his friends, but he did want to save a very good sandwich he had. This moment epitomizes Joey. He’s dumb, he’s selfish, but not harmful as long as the gunshot noises aren’t actual gunshots. If that actually are, however, you’re doomed.
2 Rachel: Convincing Bonnie to Shave Her Head
While the tumultuous Ross and Rachel love story has had its ups and downs on both sides (and that’ll be discussed soon), there aren’t a lot of moments that fall squarely on Rachel as the instigator. The biggest of these few moments, however, is Bonnie, a woman Ross starts to date.
Rachel talks with Bonnie and convinces her to shave her head in order to lessen Ross’ attraction to her. While the biggest downside could be seeing how shallow and appearance-focused Ross is, Rachel, knowing this about her former/future partner and exploiting it so she doesn’t have to see him move on, be happy, and succeed, is just cruel. Not that Ross wouldn’t self-sabotage, anyway.
1 Ross: Everything Involving Rachel
Ross is not a good boyfriend; controlling, obsessive, and philandering, Ross Gellar does about everything wrong he could possibly do in regards to his famous on-again-off-again relationship with Rachel. Saying her name at his wedding to another woman, lying about getting their Vegas marriage annulled, belittling her, manipulating her, and cheating on her are only the biggest stand-outs in a 10-year career of a toxic relationship.
For a show which mostly focuses on lies in this relationship, Friends spent a lot of time letting Ross prove himself as an unfit partner for Rachel, or for any woman, in fact. Every plan was misguided, and every moment an opportunity for infidelity or cruelty. Plus, considering how easily he’d throw any of the four other friends to the wayside in one of these schemes, Ross is not only a bad boyfriend, but a bad friend.